6-tert-Butyl-5,8-dihydroxy-2,3-dimethoxy-[1,4]naphthoquinone | 136471-22-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: 6-tert-Butyl-5,8-dihydroxy-2,3-dimethoxy-[1,4]naphthoquinone
• CAS: 136471-22-2
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: MHYZKAMVTWUFPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  93.06
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-tert-Butyl-5,8-dihydroxy-2,3-dimethoxy-[1,4]naphthoquinone 在 三氯化铝 作用下， 以 硝基苯 为溶剂， 反应 4.0h， 以94%的产率得到6-tert-butyl-2,3,5,8-tetrahydroxynaphthalene-1,4-dione
  参考文献：
  名称：

  Synthesis of some hydroxynaphthazarins and their cardioprotective effects under ischemia-reperfusion in vivo

  摘要：

  A series of hydroxynaphthazarins has been synthesized. Some of them were found in in vivo experiments to be protectors of myocardium under ischemia-reperfusion and to reduce the infarction zone by 50% without any adverse effect. All compounds exhibit a moderate or small toxicity and are active in low doses. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00075-4
• 作为产物：
  描述：

  2-叔丁基-1,4-二甲氧基苯 在 aluminum oxide 、 三氯化铝 、 cesium fluoride 、 sodium chloride 作用下， 反应 8.08h， 生成 6-tert-Butyl-5,8-dihydroxy-2,3-dimethoxy-[1,4]naphthoquinone
  参考文献：
  名称：

  Synthesis of some hydroxynaphthazarins and their cardioprotective effects under ischemia-reperfusion in vivo

  摘要：

  A series of hydroxynaphthazarins has been synthesized. Some of them were found in in vivo experiments to be protectors of myocardium under ischemia-reperfusion and to reduce the infarction zone by 50% without any adverse effect. All compounds exhibit a moderate or small toxicity and are active in low doses. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00075-4

文献信息

• Fluoride salts-alcohols-alumina as reagents for nucleophilic substitution of chlorine atoms for alkoxy groups in 2,3-dichlorosubstituted juglones, naphthazarines, and quinizarines
  作者：Victor Ph. Anufriev、Vyacheslav L. Novikov

  DOI：10.1016/0040-4039(95)00295-n

  日期：1995.4

  Direct displacement of chlorine atoms by alkoxy groups in 2,3-dichlorosubstituted juglones (5-hydroxy-1,4-naphthoquinones), naphthazarines (5,8-dihydroxy-1,4-naphthoquinones), and quinizarines (1,4-dihydroxy-9,10-anthraquinones) is generally ineffective, however high yields are obtained when methanol or cellosolves activated by fluoride anion are used as nucleophiles and the reaction goes in the presence

  2,3-二氯取代的聚对二甲苯（5-羟基-1,4-萘醌），萘萘烷（5,8-二羟基-1,4-萘醌）和喹唑啉（1,4-二羟基）中的烷氧基直接取代氯原子（-9，10-蒽醌）通常无效，但是当将甲醇或由氟阴离子活化的溶纤剂用作亲核试剂并且反应在氧化铝的存在下进行时，可获得高产率。
• Catalytic activity of sorbents containing metals, and nucleophilicity of alcohols activated with fluoride anion in reaction of nucleophilic substitution in 2,3-dichloronaphthazarines
  作者：G. V. Malinovskaya、V. F. Anufriev、V. P. Glazunov

  DOI：10.1007/bf02757441

  日期：2000.6

  In reaction of 5,8-dihydroxy-2,3-dichloro-6-ethyl-7-ethoxy-1,4-naphthoquinone and 6-tert-butyl-5,8-dihydroxy-2,3-dichloro-1,4-naphthoquinone proceeding on the surface of molecular sieves, calcium phosphate and carbonate, neutral alumina, or magnesium silicate with nucleophilic reagents (methanol, 2-methoxyethanol, monomethyl ethers of di- and triethylene glycols) activated with fluoride anion the yield of products decreased in this nucleophiles series. The most active catalysts among sorbents are alumina and magnesium silicate. All the sorbents are also efficient catalysts of alkoxy groups interchange.